CA2352125A1 - Adhesives with epoxy resin having allyl or vinyl groups - Google Patents
Adhesives with epoxy resin having allyl or vinyl groups Download PDFInfo
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- CA2352125A1 CA2352125A1 CA002352125A CA2352125A CA2352125A1 CA 2352125 A1 CA2352125 A1 CA 2352125A1 CA 002352125 A CA002352125 A CA 002352125A CA 2352125 A CA2352125 A CA 2352125A CA 2352125 A1 CA2352125 A1 CA 2352125A1
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- vinyl
- weight
- present
- allyl
- adhesive composition
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-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J201/00—Adhesives based on unspecified macromolecular compounds
- C09J201/02—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/064—Polymers containing more than one epoxy group per molecule
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L24/00—Arrangements for connecting or disconnecting semiconductor or solid-state bodies; Methods or apparatus related thereto
- H01L24/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L24/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
- H01L24/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
- H01L24/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/10—Details of semiconductor or other solid state devices to be connected
- H01L2924/102—Material of the semiconductor or solid state bodies
- H01L2924/1025—Semiconducting materials
- H01L2924/10251—Elemental semiconductors, i.e. Group IV
- H01L2924/10253—Silicon [Si]
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/10—Details of semiconductor or other solid state devices to be connected
- H01L2924/11—Device type
- H01L2924/14—Integrated circuits
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/15—Details of package parts other than the semiconductor or other solid state devices to be connected
- H01L2924/151—Die mounting substrate
- H01L2924/156—Material
- H01L2924/157—Material with a principal constituent of the material being a metal or a metalloid, e.g. boron [B], silicon [Si], germanium [Ge], arsenic [As], antimony [Sb], tellurium [Te] and polonium [Po], and alloys thereof
- H01L2924/15738—Material with a principal constituent of the material being a metal or a metalloid, e.g. boron [B], silicon [Si], germanium [Ge], arsenic [As], antimony [Sb], tellurium [Te] and polonium [Po], and alloys thereof the principal constituent melting at a temperature of greater than or equal to 950 C and less than 1550 C
- H01L2924/15747—Copper [Cu] as principal constituent
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/15—Details of package parts other than the semiconductor or other solid state devices to be connected
- H01L2924/181—Encapsulation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Die Bonding (AREA)
- Epoxy Resins (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Adhesive compositions containing a base resin and an epoxy resin with allyl or vinyl functionality show enhanced adhesive strength. The compositions can be used in microelectronic applications.
Description
ADHESIVES WITH EPOXY RESIN HAVING ALLYL OR VINYL GROUPS
This invention relates to die attach adhesives with improved adhesion due to the presence of epoxy resin with allyl or vinyl unsaturation.
Adhesive compositions are used for a variety of purposes in the fabrication and assembly of semiconductor packages, such as, the bonding of integrated circuit chips to leadframes or other substrates, and the bonding of circuit packages or assemblies to printed wire boards. Major requirements for these uses are fast cure and high adhesive strength, traditionally achieved with epoxy resins. Epoxy resins, however, can be brittle, and other resins have been evaluated and employed to bring flexibility, hydrophobicity, and other properties to die attach adhesives. The alternate resins, in turn, do not always display the strong adhesion provided by the epoxy resins. Therefore, there is a need for die attach adhesives that incorporate a balance of properties to meet all the requirements for an adhesive used in the manufacture of a semiconductor package.
This invention is an adhesive composition comprising (a) a resin capable of cure by free-radical polymerization, that is, having carbon to carbon unsaturation, or capable of cure by hydrosilation, that is, having silicon-hydride groups, (b} an epoxy compound that contains allyl or vinyl unsaturation, (c) a curing agent for the resin and a curing agent for the epoxy, and (d) optionally, one or more fillers. The composition may also contain adhesion promoters or coupling agents. The inventors discovered that the addition of the epoxy compound containing allyl or vinyl unsaturation gave an 5 unexpected increase in adhesion performance to the base resin containing the carbon to carbon unsaturation. In another embodiment, this invention is a semiconductor package having a semiconductor die adhered to a substrate with the inventive adhesive.
Free-radical curable resins, which can be used as adhesives in microelectronic applications, include, for example, maleimides, such as those available from Ciba Specialty Chemicals; siloxanes and polysiloxanes, such as those available from from Gelest; polyethers, such as those available from from BASF; polyesters, such as those available from from Uniqema or Bayer;
poly(butadiene)s, such as those available from from Elf-Atochem;
polyurethanes, such as those available from from Bayer or BASF; and acrylate resins, such as those available from from Sartomer or UCB Radcure.
Siloxanes and polysiloxanes, which cure by hydrosilation, may be linear or cylic polymers, and will have at least 2 silicone-hydride functionalities per molecule. The polyethers, polyesters, and polyurethanes preferably will contain terminal unsaturation, but may also contain unsaturation within the polymer chain. The particular resin will be chosen by the practitioner to give specific material properties in a final formulation, such as, rheological properties, hydrophilic or hydrophobic properties, toughness, strength, or flexibility. The resin will be present in the adhesive composition in a range of 10-80% by weight.
The epoxy compounds may be any epoxy compounds with allyl or vinyl functionality. Examples include 2,6-digylcidyl phenyl allyl ether, limonene dioxide, glycidyl vinyl benzyl ether or glycidyl vinyl ether. The epoxy will be present in the adhesive composition in a range of 0.1-30% by weight.
Exemplary curing agents for the base resins are free-radical initiators, which can be thermal- or photo-initiators. The initiators will be present in the adhesive composition in an amount of 0.1 % to 10%, preferably 0.1 % to 3.0%, by weight. Preferred thermal initiators include peroxides, such as butyl peroctoates and dicumyl peroxide, and azo compounds, such as 2,2'-azobis(2-methyl-propanenitrile) and 2,2'-azobis(2-methyl-butanenitrile).
A preferred series of photoinitiator is one sold under the trademark Irgacure by Ciba Specialty Chemicals. In some formulations, both photo-cure and thermal cure may be desirable, for example, the curing process can be started by irradiation, and in a later processing step curing can be completed by the application of heat.
Exemplary curing agents for the epoxy functionality on the epoxy resin are Lewis bases, for example, amines, such as Ancamine 2337xs, and 4,4'-bis(para amino cyclohexyl) methane, both commercially available from Air Products; imidazoles, such as Curezol 2E4MZ-CN, a product of Shikoku Chemicals; amides, such as, Dicyanamide, a product of Air Products;
polyamides, such as Versamide 140, a product of Henkel; tertiary amines, such as Amicure DBU, a product of Air Products. Alternatively, Lewis acids, such as Rhodorasil 2074 [(tolylcumyl) iodonium tetrakis (pentafluorophenyl) borate], a product of Rhodia, or GE UV9380C, a product of General Electric, can be used to initiate a cationic cure. The curing agent for the epoxy functionality will be present in the composition in a range of 0.1 to 3 % by weight of the total formulation.
In general, these compositions will cure within a temperature range of 70°C to 250°C, and curing will be effected within a range of ten seconds to three hours. The time and temperature curing profile of each formulation will vary with the components of the formulation, but the parameters of a curing profile can be adjusted by a practitioner skilled in the art without undue experimentation.
In some compositions it may be desirable to add organic or inorganic fillers. Suitable conductive fillers are carbon black, graphite, gold, silver, copper, platinum, palladium, nickel, aluminum, silicon carbide, boron nitride, diamond, and alumina. Suitable nonconductive fillers are particles of vermiculite, mica, wollastonite, calcium carbonate, titania, sand, glass, fused silica, fumed silica, barium sulfate, and halogenated ethylene polymers, such as tetrafluoroethylene, trifluoroethylene, vinylidene fluoride, vinyl fluoride, vinylidene chloride, and vinyl chloride. Although optional, when present, fillers will be in amounts of 20% to 90% by weight of the composition.
Suitable adhesion promoters or coupling agents are silanes, silicate esters, metal acrylates or methacrylates, titanates, and compounds containing a chelating ligand, such as phosphine, mercaptan, and acetoacetate. When present, coupling agents will be in amounts up to 10%
by weight, and preferably in amounts of 0.1 % to 3.0% percent by weight.
The invention is further illustrated by the following examples, which are not intended as a limitation on the invention.
Semiconductor packages, consisting of a silicon die adhered to a bond pad on a leadframe with an adhesive, the die and the leadframe encapsulated in a molding compound, are tested for reliability using a test protocol of JEDEC Solid State Technology Association identified as JESD22-A112. In this method, the semiconductor package is subjected to 85°C and 85% relative humidity for 168 hours followed by exposure to 240°C in an infared oven using a standard solder reflow vamped profile of five minutes.
Reliability failure of the package manifests itself as delamination of any of the package interfaces or as cracked molding compound.
Previous experiments of the inventors testing for failure of the adhesive adhering the die to the leadframe were conducted using 5 unencapsulated assemblies of a die adhered to a leadframe with die attach adhesives. In these experiments, the unencapsulated assemblies were cured in an oven at 175°C for 30 minutes. After cure, the assemblies were divided into two groups. The first group was tested for die shear strength after exposure to a hot dry environment, which consisted of 240°C for one minute, followed by 175°C for four hours.
The second group was tested for die shear strength after exposure to a hot wet environment, which consisted of 85% relative humidity at 85°C
for 168 hours.
After exposure, each group of assemblies was heated to 250°C, after which the die was sheared from its substrate. Some of the assemblies exhibited cohesive mode failure of the adhesive adhering the die to the leadframe, others exhibited adhesive mode failure of the adhesive adhering the die to the leadframe.
Those adhesives that failed in a cohesive mode correlated with higher reliability in the JEDEC test method on encapsulated packages using the same adhesive, while the adhesives that failed in the adhesive mode giving a clean metal surface, correlated with lower reliability in the JEDEC
test method on encapsulated packages using the same adhesive.
In the following examples, formulations with and without the epoxy with allyl or vinyl functionality were tested for hot dry die shear strength (measured in kg of force), and for hot wet die shear strength using the above described protocols. The die used was a silicon die, 12.5mm x 12.5mm x 0.38mm adhered to a bare copper or a silver-plated leadframe.
This invention relates to die attach adhesives with improved adhesion due to the presence of epoxy resin with allyl or vinyl unsaturation.
Adhesive compositions are used for a variety of purposes in the fabrication and assembly of semiconductor packages, such as, the bonding of integrated circuit chips to leadframes or other substrates, and the bonding of circuit packages or assemblies to printed wire boards. Major requirements for these uses are fast cure and high adhesive strength, traditionally achieved with epoxy resins. Epoxy resins, however, can be brittle, and other resins have been evaluated and employed to bring flexibility, hydrophobicity, and other properties to die attach adhesives. The alternate resins, in turn, do not always display the strong adhesion provided by the epoxy resins. Therefore, there is a need for die attach adhesives that incorporate a balance of properties to meet all the requirements for an adhesive used in the manufacture of a semiconductor package.
This invention is an adhesive composition comprising (a) a resin capable of cure by free-radical polymerization, that is, having carbon to carbon unsaturation, or capable of cure by hydrosilation, that is, having silicon-hydride groups, (b} an epoxy compound that contains allyl or vinyl unsaturation, (c) a curing agent for the resin and a curing agent for the epoxy, and (d) optionally, one or more fillers. The composition may also contain adhesion promoters or coupling agents. The inventors discovered that the addition of the epoxy compound containing allyl or vinyl unsaturation gave an 5 unexpected increase in adhesion performance to the base resin containing the carbon to carbon unsaturation. In another embodiment, this invention is a semiconductor package having a semiconductor die adhered to a substrate with the inventive adhesive.
Free-radical curable resins, which can be used as adhesives in microelectronic applications, include, for example, maleimides, such as those available from Ciba Specialty Chemicals; siloxanes and polysiloxanes, such as those available from from Gelest; polyethers, such as those available from from BASF; polyesters, such as those available from from Uniqema or Bayer;
poly(butadiene)s, such as those available from from Elf-Atochem;
polyurethanes, such as those available from from Bayer or BASF; and acrylate resins, such as those available from from Sartomer or UCB Radcure.
Siloxanes and polysiloxanes, which cure by hydrosilation, may be linear or cylic polymers, and will have at least 2 silicone-hydride functionalities per molecule. The polyethers, polyesters, and polyurethanes preferably will contain terminal unsaturation, but may also contain unsaturation within the polymer chain. The particular resin will be chosen by the practitioner to give specific material properties in a final formulation, such as, rheological properties, hydrophilic or hydrophobic properties, toughness, strength, or flexibility. The resin will be present in the adhesive composition in a range of 10-80% by weight.
The epoxy compounds may be any epoxy compounds with allyl or vinyl functionality. Examples include 2,6-digylcidyl phenyl allyl ether, limonene dioxide, glycidyl vinyl benzyl ether or glycidyl vinyl ether. The epoxy will be present in the adhesive composition in a range of 0.1-30% by weight.
Exemplary curing agents for the base resins are free-radical initiators, which can be thermal- or photo-initiators. The initiators will be present in the adhesive composition in an amount of 0.1 % to 10%, preferably 0.1 % to 3.0%, by weight. Preferred thermal initiators include peroxides, such as butyl peroctoates and dicumyl peroxide, and azo compounds, such as 2,2'-azobis(2-methyl-propanenitrile) and 2,2'-azobis(2-methyl-butanenitrile).
A preferred series of photoinitiator is one sold under the trademark Irgacure by Ciba Specialty Chemicals. In some formulations, both photo-cure and thermal cure may be desirable, for example, the curing process can be started by irradiation, and in a later processing step curing can be completed by the application of heat.
Exemplary curing agents for the epoxy functionality on the epoxy resin are Lewis bases, for example, amines, such as Ancamine 2337xs, and 4,4'-bis(para amino cyclohexyl) methane, both commercially available from Air Products; imidazoles, such as Curezol 2E4MZ-CN, a product of Shikoku Chemicals; amides, such as, Dicyanamide, a product of Air Products;
polyamides, such as Versamide 140, a product of Henkel; tertiary amines, such as Amicure DBU, a product of Air Products. Alternatively, Lewis acids, such as Rhodorasil 2074 [(tolylcumyl) iodonium tetrakis (pentafluorophenyl) borate], a product of Rhodia, or GE UV9380C, a product of General Electric, can be used to initiate a cationic cure. The curing agent for the epoxy functionality will be present in the composition in a range of 0.1 to 3 % by weight of the total formulation.
In general, these compositions will cure within a temperature range of 70°C to 250°C, and curing will be effected within a range of ten seconds to three hours. The time and temperature curing profile of each formulation will vary with the components of the formulation, but the parameters of a curing profile can be adjusted by a practitioner skilled in the art without undue experimentation.
In some compositions it may be desirable to add organic or inorganic fillers. Suitable conductive fillers are carbon black, graphite, gold, silver, copper, platinum, palladium, nickel, aluminum, silicon carbide, boron nitride, diamond, and alumina. Suitable nonconductive fillers are particles of vermiculite, mica, wollastonite, calcium carbonate, titania, sand, glass, fused silica, fumed silica, barium sulfate, and halogenated ethylene polymers, such as tetrafluoroethylene, trifluoroethylene, vinylidene fluoride, vinyl fluoride, vinylidene chloride, and vinyl chloride. Although optional, when present, fillers will be in amounts of 20% to 90% by weight of the composition.
Suitable adhesion promoters or coupling agents are silanes, silicate esters, metal acrylates or methacrylates, titanates, and compounds containing a chelating ligand, such as phosphine, mercaptan, and acetoacetate. When present, coupling agents will be in amounts up to 10%
by weight, and preferably in amounts of 0.1 % to 3.0% percent by weight.
The invention is further illustrated by the following examples, which are not intended as a limitation on the invention.
Semiconductor packages, consisting of a silicon die adhered to a bond pad on a leadframe with an adhesive, the die and the leadframe encapsulated in a molding compound, are tested for reliability using a test protocol of JEDEC Solid State Technology Association identified as JESD22-A112. In this method, the semiconductor package is subjected to 85°C and 85% relative humidity for 168 hours followed by exposure to 240°C in an infared oven using a standard solder reflow vamped profile of five minutes.
Reliability failure of the package manifests itself as delamination of any of the package interfaces or as cracked molding compound.
Previous experiments of the inventors testing for failure of the adhesive adhering the die to the leadframe were conducted using 5 unencapsulated assemblies of a die adhered to a leadframe with die attach adhesives. In these experiments, the unencapsulated assemblies were cured in an oven at 175°C for 30 minutes. After cure, the assemblies were divided into two groups. The first group was tested for die shear strength after exposure to a hot dry environment, which consisted of 240°C for one minute, followed by 175°C for four hours.
The second group was tested for die shear strength after exposure to a hot wet environment, which consisted of 85% relative humidity at 85°C
for 168 hours.
After exposure, each group of assemblies was heated to 250°C, after which the die was sheared from its substrate. Some of the assemblies exhibited cohesive mode failure of the adhesive adhering the die to the leadframe, others exhibited adhesive mode failure of the adhesive adhering the die to the leadframe.
Those adhesives that failed in a cohesive mode correlated with higher reliability in the JEDEC test method on encapsulated packages using the same adhesive, while the adhesives that failed in the adhesive mode giving a clean metal surface, correlated with lower reliability in the JEDEC
test method on encapsulated packages using the same adhesive.
In the following examples, formulations with and without the epoxy with allyl or vinyl functionality were tested for hot dry die shear strength (measured in kg of force), and for hot wet die shear strength using the above described protocols. The die used was a silicon die, 12.5mm x 12.5mm x 0.38mm adhered to a bare copper or a silver-plated leadframe.
The adhesive composition and performance test data are set out in the following tables and show that the adhesive formulations containing epoxy with allyl or vinyl functionality failed during hot wet die shear testing in a cohesive mode, while the formulations without the epoxy containing allyl or vinyl functionality failed in an adhesive mode. Therefore, the data indicate that the formulations containing the epoxy compound with vinyl or allyl unsaturation improve adhesive performance and semiconductor package reliability. The compositions are reported in weight percent.
With With epoxy epoxy resin resin with COMPOSITION Ex.1 allyl without functionality allyl functionali proprietary bismaleimide19.04% 19.04%
I
4,4'-bismaleimido- 0.52% 0.52%
I
di hen (methane ~ (2,6-digylcidylphenyl1.2% ---allyl ether a ox resin I
bis-phenol-F epoxy ---- 1.57%
resin '~I poly(budadiene) 2.61 2.61 (Ricon 130) %
polyester vinyl ether1.57% 1.57%
resin Allied si nal VE1312 I adduct of cinnamyl3.39% 3.39%
alcohol with ' dimer diisoc anate i, methacryloxy silane0.4% 0.4%
Witco A-174 I
i 1,1-di(t-amyl peroxy)0.65% 0.65%
j cyclohexane Witco USP90MD
i 2-ethyl 4-methyl 0.25% 0.25%
imidazole-CN
I
i silver flake 70% 70%
i Total 100% 100%
I
Silver- Bare Silver- Bare PERFORMANCE Ex.1 plated Copper plated Copper leadframeleadframeleadframeleadframe I
'~ Cured for 30 minutes/175C15.5N 8.3p 18.6N 7.1 N
' Die war a a RT i Hot Dry Die Shear 14.1kg 12.3kg 1.3 kg 1.8 kg @ 250C
cohesivecohesiveadhesiveadhesive ' Hot Wet Die Shear 7.3 kg 6.24 1.3 kg 1.6 kg @ 250C kg i cohesivecohesiveadhesiveadhesive With With epoxy epoxy resin resin with COMPOSITION EX.2 allyl without functionality ally) functionalit polybutadiene with 10.5% 10.5%
acrylate functionalit Ricon, polybutadiene with 2.0% 2.0%
malefic anhydride functionality Ricon, 130MA10 1,6-diol diacrylate 2.0% 2.0%
Sartomer SR238 isobornyl acrylate 5.0% 5.0%
Sartomer SR506 1,1-di(t-amyl peroxyl)0.5% 0.5%
cyclohexane Witco USP, 90MD
lauryl acrylate 2.5% 2.5%
Sartomer SR335 2,6-diglycidylphenyl 2.0% 0%
allyl ether 2-ethyl 4-methyl imidazole-CN0.2% 0%
silver flake 75% 75%
Total 100% 100%
Silver-Bare Silver- Bare PERFORMANCE Ex.2 plated Copper plated Copper leadframeleadframeleadframeleadframe Die Warpage at room temp.
Cured for 30 minutes/175C 22.5N 17.ON
Plus 1 minute/220C 26.6N 17.5 or N
Plus 4 hoursl174C 19.7N 12.1 N
'delaminated Hot Dry Die Shear 6.6kg l.3kg @ 250C
failure mode cohesive adhesive Hot Wet Die Shear 2.8kg 1kg @ 250C
failure mode cohesive adhesive Note:
Adhesion to Ag-plated leadframe was satisfactory for both formulations.
COMPOSITION Ex.3 With epoxy resinWith epoxy resin with allyl functionalitywithout allyl functionali S car resin * 13.96 11.56 Polybutadiene 2.33 1.93 Ricon Resins, Ricon Poly(butadiene) functionalized1.4 1.16 with malefic anhydride (Ricon Resins, Ricon Poly(butadiene) functionalized0.23 0.20 with malefic anhydride (Ricon Resins, Ricon Diallyl bisphenol-A 1.63 1.35 Bi-Max Divinyl ether 1.16 0.96 ISP Tech, DVE-3 (2,6-diglycidylphenyl---- 2.90 allyl ether a ox 1,3-bis (glycidoxypropyl)---- 0.58 -tetramethyldisiloxane Gelest, SIB 1115.0 Rhodorsil 2074 ---- 0.6 Rhone Poulenc fumed silica 0.5 0.5 De ussa, 812S
silver powder 78 78 Chemet, K-0082P
platinum complex* 0.4 0.4 Sivento Inc., CPC
platinum complex' 0.4 0.4 Sivento Inc. CPS 925-P
Total 100% 100%
PERFORMANCE Ex. 3*' Die Shear Strength 17.0 1.5 15.33.2 @200C, 360x360 mil Si die on PBGA
after 48hrs at 85/85 Failure mode Adhesive to Peel off 80%
die solder backside mask 'The stock solution as received was diluted with cyclic methylvinylsiloxanes to achieve -5000ppm Pt concentration.
'* The adhesive compositions were dispensed on a metal lead frame and cured in a convection oven by vamping from room temperature to 175C over 30 minutes then holding at 175C for 15 minutes.
With With epoxy epoxy resin resin with COMPOSITION Ex.1 allyl without functionality allyl functionali proprietary bismaleimide19.04% 19.04%
I
4,4'-bismaleimido- 0.52% 0.52%
I
di hen (methane ~ (2,6-digylcidylphenyl1.2% ---allyl ether a ox resin I
bis-phenol-F epoxy ---- 1.57%
resin '~I poly(budadiene) 2.61 2.61 (Ricon 130) %
polyester vinyl ether1.57% 1.57%
resin Allied si nal VE1312 I adduct of cinnamyl3.39% 3.39%
alcohol with ' dimer diisoc anate i, methacryloxy silane0.4% 0.4%
Witco A-174 I
i 1,1-di(t-amyl peroxy)0.65% 0.65%
j cyclohexane Witco USP90MD
i 2-ethyl 4-methyl 0.25% 0.25%
imidazole-CN
I
i silver flake 70% 70%
i Total 100% 100%
I
Silver- Bare Silver- Bare PERFORMANCE Ex.1 plated Copper plated Copper leadframeleadframeleadframeleadframe I
'~ Cured for 30 minutes/175C15.5N 8.3p 18.6N 7.1 N
' Die war a a RT i Hot Dry Die Shear 14.1kg 12.3kg 1.3 kg 1.8 kg @ 250C
cohesivecohesiveadhesiveadhesive ' Hot Wet Die Shear 7.3 kg 6.24 1.3 kg 1.6 kg @ 250C kg i cohesivecohesiveadhesiveadhesive With With epoxy epoxy resin resin with COMPOSITION EX.2 allyl without functionality ally) functionalit polybutadiene with 10.5% 10.5%
acrylate functionalit Ricon, polybutadiene with 2.0% 2.0%
malefic anhydride functionality Ricon, 130MA10 1,6-diol diacrylate 2.0% 2.0%
Sartomer SR238 isobornyl acrylate 5.0% 5.0%
Sartomer SR506 1,1-di(t-amyl peroxyl)0.5% 0.5%
cyclohexane Witco USP, 90MD
lauryl acrylate 2.5% 2.5%
Sartomer SR335 2,6-diglycidylphenyl 2.0% 0%
allyl ether 2-ethyl 4-methyl imidazole-CN0.2% 0%
silver flake 75% 75%
Total 100% 100%
Silver-Bare Silver- Bare PERFORMANCE Ex.2 plated Copper plated Copper leadframeleadframeleadframeleadframe Die Warpage at room temp.
Cured for 30 minutes/175C 22.5N 17.ON
Plus 1 minute/220C 26.6N 17.5 or N
Plus 4 hoursl174C 19.7N 12.1 N
'delaminated Hot Dry Die Shear 6.6kg l.3kg @ 250C
failure mode cohesive adhesive Hot Wet Die Shear 2.8kg 1kg @ 250C
failure mode cohesive adhesive Note:
Adhesion to Ag-plated leadframe was satisfactory for both formulations.
COMPOSITION Ex.3 With epoxy resinWith epoxy resin with allyl functionalitywithout allyl functionali S car resin * 13.96 11.56 Polybutadiene 2.33 1.93 Ricon Resins, Ricon Poly(butadiene) functionalized1.4 1.16 with malefic anhydride (Ricon Resins, Ricon Poly(butadiene) functionalized0.23 0.20 with malefic anhydride (Ricon Resins, Ricon Diallyl bisphenol-A 1.63 1.35 Bi-Max Divinyl ether 1.16 0.96 ISP Tech, DVE-3 (2,6-diglycidylphenyl---- 2.90 allyl ether a ox 1,3-bis (glycidoxypropyl)---- 0.58 -tetramethyldisiloxane Gelest, SIB 1115.0 Rhodorsil 2074 ---- 0.6 Rhone Poulenc fumed silica 0.5 0.5 De ussa, 812S
silver powder 78 78 Chemet, K-0082P
platinum complex* 0.4 0.4 Sivento Inc., CPC
platinum complex' 0.4 0.4 Sivento Inc. CPS 925-P
Total 100% 100%
PERFORMANCE Ex. 3*' Die Shear Strength 17.0 1.5 15.33.2 @200C, 360x360 mil Si die on PBGA
after 48hrs at 85/85 Failure mode Adhesive to Peel off 80%
die solder backside mask 'The stock solution as received was diluted with cyclic methylvinylsiloxanes to achieve -5000ppm Pt concentration.
'* The adhesive compositions were dispensed on a metal lead frame and cured in a convection oven by vamping from room temperature to 175C over 30 minutes then holding at 175C for 15 minutes.
Claims (4)
1. An adhesive composition comprising:
(a) a resin capable of curing by free-radical polymerization or by hydrosilation, present in an amount of 10% to 80% by weight, (b) an epoxy compound having vinyl or allyl functionality, present in an amount of 0.1% to 30% by weight, (c) a curing agent for the epoxy compound, present in an amount of 0.1 % to 3%
by weight, (d) a curing agent for the resin, present in an amount of 0.1% to 10% by weight, and (e) optionally, a filler, present in an amount of 20% to 90% by weight.
(a) a resin capable of curing by free-radical polymerization or by hydrosilation, present in an amount of 10% to 80% by weight, (b) an epoxy compound having vinyl or allyl functionality, present in an amount of 0.1% to 30% by weight, (c) a curing agent for the epoxy compound, present in an amount of 0.1 % to 3%
by weight, (d) a curing agent for the resin, present in an amount of 0.1% to 10% by weight, and (e) optionally, a filler, present in an amount of 20% to 90% by weight.
2. The adhesive composition according to claim 1 in which the resin is selected from the group consisting of maleimides, polyethers, polyesters, poly(butadiene)s, polyurethanes, acrylates, siloxanes, and polysiloxanes.
3. The adhesive composition according to claim 1 in which the epoxy compound is selected from the group consisting of 2,6-digylcidylphenyl allyl ether, limonene dioxide, glycidyl vinyl benzyl ether, and gylcidyl vinyl ether.
4. The adhesive composition according to claim 1 in which the filler is present and is selected from the group consisting of carbon black, graphite, gold, silver, copper, platinum, palladium, nickel, aluminum, silicon carbide, boron nitride, diamond, alumina, vermiculite, mica, wollastonite, calcium carbonate, titania, sand, glass, fused silica, fumed silica, barium sulfate, tetrafluoroethylene, trifluoroethylene, vinylidene fluoride, vinyl fluoride, vinylidene chloride, and vinyl chloride.
The use of an adhesive composition as claimed in any of claims 1 to 4 as a die attach adhesive.
The use of an adhesive composition as claimed in any of claims 1 to 4 as a die attach adhesive.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/611,899 | 2000-07-07 | ||
| US09/611,899 US6750301B1 (en) | 2000-07-07 | 2000-07-07 | Die attach adhesives with epoxy compound or resin having allyl or vinyl groups |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2352125A1 true CA2352125A1 (en) | 2002-01-07 |
Family
ID=24450834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002352125A Abandoned CA2352125A1 (en) | 2000-07-07 | 2001-07-04 | Adhesives with epoxy resin having allyl or vinyl groups |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6750301B1 (en) |
| EP (1) | EP1170346B1 (en) |
| JP (1) | JP4541599B2 (en) |
| KR (1) | KR100794636B1 (en) |
| CN (1) | CN1193081C (en) |
| CA (1) | CA2352125A1 (en) |
| DE (1) | DE60109366T2 (en) |
| HK (1) | HK1043382B (en) |
| SG (1) | SG99913A1 (en) |
| TW (1) | TWI225513B (en) |
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-
2000
- 2000-07-07 US US09/611,899 patent/US6750301B1/en not_active Expired - Lifetime
-
2001
- 2001-07-04 EP EP01115670A patent/EP1170346B1/en not_active Expired - Lifetime
- 2001-07-04 JP JP2001203485A patent/JP4541599B2/en not_active Expired - Fee Related
- 2001-07-04 DE DE60109366T patent/DE60109366T2/en not_active Expired - Lifetime
- 2001-07-04 CA CA002352125A patent/CA2352125A1/en not_active Abandoned
- 2001-07-04 TW TW090116527A patent/TWI225513B/en not_active IP Right Cessation
- 2001-07-05 SG SG200104052A patent/SG99913A1/en unknown
- 2001-07-05 CN CNB011225637A patent/CN1193081C/en not_active Expired - Lifetime
- 2001-07-05 KR KR1020010040099A patent/KR100794636B1/en active IP Right Grant
-
2002
- 2002-07-10 HK HK02105140.6A patent/HK1043382B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HK1043382A1 (en) | 2002-09-13 |
| JP2002060715A (en) | 2002-02-26 |
| JP4541599B2 (en) | 2010-09-08 |
| EP1170346A3 (en) | 2002-07-24 |
| CN1332217A (en) | 2002-01-23 |
| KR20020003525A (en) | 2002-01-12 |
| CN1193081C (en) | 2005-03-16 |
| SG99913A1 (en) | 2003-11-27 |
| US6750301B1 (en) | 2004-06-15 |
| TWI225513B (en) | 2004-12-21 |
| HK1043382B (en) | 2005-11-04 |
| DE60109366D1 (en) | 2005-04-21 |
| EP1170346A2 (en) | 2002-01-09 |
| EP1170346B1 (en) | 2005-03-16 |
| KR100794636B1 (en) | 2008-01-14 |
| DE60109366T2 (en) | 2005-08-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |